Caoutchouc substance and process of making same.



UNITED STATES PATENT OFFICE.

FRITZ HOFMANN, CARL GOU'IELLE, KON RAD DELBRU'CK, AND KURT MEISENBURG,OF ELBERFELD, GERMANY, ASSIGNORS TO FARBENFABBIKEN VORM. FRIEDR. BAYER &00., OF ELBERFELD, GERMANY, A CORPORATION OFGERMANY.

CAOUTCHOU 'C SUBSTANCE AND PROCESS OF MAKING SAME.

No Drawing.

To all whom may concern:

Be it known that we, FRITZ HoFMANN, CARL CoU'rELLE, KoNRAn DE BRiioK,and KURT MEISENBURG, citizens of the German Empire, residing atElberfeld, Germany, have invented new and useful Improvements inGaoutchouc Substances and Processes of Making Same, of which thefollowing is a specification.

By our earlier applications Ser. Nos. 578607 and 588173 the productionof caout-' chouc like substances is described, which may replace naturalcaoutchouc in its chemical and technical application. The processes fortheir production consist in converting into caoutchouc like substanceserythrene or its homologues in which at least 2 atoms of H aresubstituted by methyl groups, such as di-, trior tetramethylerythre'ne.

It has now been found that by using mixtures of the starting materialsmentioned in the above applications (erythrene and its substitutionproducts) new caoutchouc-like substances can be advantageously produced,with properties different from those of the caoutchouc-like substancesabove referred to.

' Caoutchouc-like substances can be thus profully the following exampleis given, the

parts being by weight :A mixture of 100 parts ofbeta-gamma-dimethylerythrene and 100 parts of cooled erythrene is heatedfor 3 months in an autoclave to 7075 C. A very tough and elasticsubstance is thus obtained made up of the caoutchouc-like substancetogether with any remaining unchanged hydrocarbons and by-products. Bytreatment of this substance With steam such hydrocar- "bons and volatileby-products, if present, can

be removed and the caoutchouc-like substance which is insoluble inacetone obtained.

Mixtures or the different dimethylerythrenes or pr die-withtri-methylerythrenes or of diwith trif-and,tetra-methylerythrenes may beSpecification. of Letters Patent.

Patented May 27, 1913.

Application filed Hatch 20, 1911. Serial No. 615,664.

used. The new process proceeds in an analogous manner on us1ng agentspromoting the polymerization e. g. acids or acid.

are free from protein substances, which are always contained in thenatural caoutchouc and play an important part in it with regard to theelasticity of the natural caoutchouc; They form ozonids being thickoils, nitrosites and brom addition products. These ozonids, nitrositesand brom-addition products differ with the different compositecaoutchouc products, and correspond to these different products, andthus indirectly to the particular mixtures of hydrocarbons of which thecomposite caoutchoucs are polymerization products. Thus the productproduced as above described from a mixture of beta-gamma-dimethylerythrene and erythrene forms an ozonid, or mixture of ozonids, which,upon decomposition with water yields a mixture of oxygen-containingdecomposition products among which succinic aldehyde and acetonylacetone (a dimethyl derivativeof succinic' aldehyde) are found.

We claim 1. The process of producing a caoutchouclike substance whichcomprises polymerizing a mixture of erythrene hydrocarbons includingerythrene.

2. The process of producing a caoutchouclike substance which comprisespolymeriiing a mixture of erythrene hydrocarbons including erythrene anda poly-methyl substituted erythrene.

3. The process of producing a caoutchouclike substance which comprisespolymerizing a mixture of erythrene hydrocarbons including erythrene anda dimethy1-eryth 5. The process of producing a caoutchouc-.

like [substance which comprlses heating a mixture of erythrenehydrocarbons includmg erythrene under caoutchouc-formmg conditionsuntila caoutchouc-like product ing erythrene and a dimethyl-erythrene un-.

der caoutchouc-forming conditions until a caoutchouc-like productresults insoluble in acetone.

8. The process of producing a caoutchouclike substance which comprisesheating a mixture of erythrene hydrocarbons including erythrene anddiisopropenyl under caoutchouc-forming conditions until acaoutchouc-likeproduct results insoluble in acetone.

9. The process of producing a caoutchouclike substance which comprisesheating in the presence of an agent promoting polymerization a mixtureof erythrene hydrocarbons including erythrene under caoutchouc-form ingconditions until a caoutchouc-like product results insoluble in acetone.

10. The process of producing a caoutchouc-like substance which comprisesheating in the presence of an agent promoting polymerization a mixtureof erythrene hydrocarbons including erythrene and a polymethylsubstituted erythrene under caoutchouc-forming conditions until acaoutchouc-like product results insoluble in acetone.

11. The process of producing a caoutchouc-like substance which comprisesheating in the presence of an agent promoting polymerization a mixtureof erythrene hydrocarbons including erythrene and a di-'methyl-erythrene under caout'chouc-forming conditions until acaoutchouc-like product results insoluble in acetone.

12. The process of producing a caout chouc-like substance whichcomprises heating in the presence of an agent promoting polymerization amixture of erythrene hydrocarbons including erythrene anddiisosubstituted erythrene which product forms a nitrosite, ozonid andbrom-addition prodnot, the ozonid upon decomposition with water yieldinga plurality of oxygen-containing decomposition products includingsuccinic aldehyde and a polymethyl substituted derivative of succinicaldehyde.

15. As a new product a caoutchouc like substance comprising thepolymerization product of a mixture of erythrene hydrocarbons includingerythrene anda dimethylsubstituted erythrene which product forms anitrosite, ozonid and brom-addition product, the ozonid upondecomposition with Water yielding a plurality of oxygen-containingdecomposition products including succinic aldehyde and a dimethylsubstituted derivative of succinic aldehyde.

16. As a new product a caout-chouc-like substancev comprising thepolymerization product of a mixture of erythrene hydrocarbons includingerythrene and diisopropenyl which product forms a nitrosite, ozonid andbrom-addition product, the ozonid upon decomposition with water yieldinga plurality of oXyen-containing decomposition products includingsuccinic aldehyde and acetonyl acetone.

In testimony whereof we have hereunto set our hands in the presence oftwo sub- 0 scribing witnesses.

FRITZ HOFMANN. [L. s.] CARL COUTELLE. [L.s.] KONRAD DELBRUCK. [L. sl]KURT MEISENBURG. [n.sL] Witnesses:

ALFRED HENKEL, A. POSEN.

